
Holiday rentals in Cockpit Island
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Top-rated holiday rentals in Cockpit Island
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Jungle Dome on a Farm! Animal Lovers Dream!
Jungle Dome Farm Stay in Burlington! Be completely immersed in farm life and all that it entails while staying in our 500 square foot geodesic dome “glamping” greenhouse dwelling! Complete with a fish and turtle pond and filled to the brim with tropical plants! Designed as a tropical vacation getaway when you can’t get away to the tropics! Situated on a 5 acre animal farm where guests can experience farm life with goats, horses, highland cows, sheep, pigs and poultry. An Animal Lovers Dream!
4.97 out of 5 average rating, 275 reviews
Private Suite Near Locke St
Enjoy a cozy experience at this centrally located place in a peaceful neighbourhood. Private entrance to a separate apartment. 2 bed 1 bathroom unit on the upper floors of a detached home. The main floor is occupied but there is no shared spaces. Located steps from Locke Street where you can find lots of trendy restaurants, cafe's and shopping. Park located within walking distance. Please review parking information. McMaster University and Children's Hospital within a 10-15 minute drive.
4.93 out of 5 average rating, 110 reviews
Frenchman’s Pass - Cozy nook on the Hamilton brow
Welcome to your home away from home! This charming suite on the main floor of our home has a separate entrance and a private deck. Nestled on the Hamilton Mountain in one of Hamilton's most upscale neighborhoods, we are steps from the scenic brow offering the perfect blend of tranquility and convenience. High-speed Wi-Fi, smart TV, private, on-site parking and essentials for a relaxing stay. Situated centrally, you're just minutes from hospitals, shopping, restaurants, and public transit.
4.86 out of 5 average rating, 189 reviews
Fully-Furnished Boutique 1 Bedroom Suites
The Laundry Rooms is situated on one of our favourite streets in Hamilton. Featuring cozy pubs, local coffee shops, and a 10-minute walk from the downtown core, Augusta Street has a small-town vibe in the heart of the city. Live like a local with all the comforts and amenities of home in our contemporary suites designed for the professional traveller. Pets are welcome and we can't wait to meet your dog (a deep cleaning fee applies (except for assistance animals))... and you, of course.
4.79 out of 5 average rating, 402 reviews
Luxury Locke Street Loft
Stay in a beautifully renovated, two-level private loft in the heart of Hamilton. Located in a historic building on trendy Locke Street, you’re minutes from top restaurants, shops, and attractions. The space features 3 bedrooms and 2 full bathrooms, sleeping up to 8 guests. Enjoy an open-concept living area with a bar setup and 85” TV, plus free parking, in-suite laundry, and exclusive discounts at Beasley’s Bistro. Perfect for relaxing or entertaining after a day exploring the city.
4.99 out of 5 average rating, 97 reviews
Chic Oasis | Steps Away From TD Coliseum Hamilton
Step into a stunning modern-retro escape where bold red tones, playful pink accents, and vintage exposed red bricks create an unforgettable vibe. Perfectly located just steps from vibrant Hess Village, you're within walking distance to concerts, sports venues, art galleries, boutiques, and top-tier dining. Explore trendy Locke Street or hike the Escarpment nearby. With cozy bedrooms, chic outdoor spaces, and irresistible charm, this gem is a true city retreat.
4.85 out of 5 average rating, 213 reviews
Summertime! Steam shower+breakfast+rooftop hottub
Nestled in a picturesque escarpment community overlooking the historic town of Dundas, The Hayloft is a charming getaway for anyone looking for an escape and a breath of fresh air. Relax in the steam shower inside or the hot tub on the fully private rooftop deck overlooking gardens. Take a nap on the lounge chairs. Visit with the chickens, make friends with the fish or the frogs. Unwind at night with a movie in bed, with breakfast (surcharge) in the morning.
4.99 out of 5 average rating, 87 reviews
Private Top-Floor Loft • Prime Hamilton Location
Bright, private top-floor suite in central Hamilton, just steps from Locke St and 2 blocks to the TD Coliseum. Walk to cafés, restaurants, and events at Bridgeworks, or explore nearby breweries, trails, and waterfalls. Only 3.5 km to McMaster University, 45 mins to Toronto, and 1 hr to Niagara Falls. Includes dedicated on-site parking. Hosted by an experienced Superhost offering a comfortable, reliable stay for both business and leisure travellers.
4.91 out of 5 average rating, 615 reviews
Waterfront Hillside Villa
Welcome to your stunning Hillside Villa situated on 150' of waterfront. Enjoy the peaceful surroundings and quiet Bay views from your 3 private outdoor decks & hot tub. Entertaining is easy in this gourmet kitchen, which is open to 1 of 2 fireplaces, family room & dining room with floor to ceiling views of the Bay. Breathe taking views of the Bay from your private dock. Hidden gems: gym, 2nd kitchen, foosball table, EV charging and private trail.
4.92 out of 5 average rating, 188 reviews
Gallery Suite
The Gallery Suite near Locke St. and McMaster is ideal for business or leisure stays. This bright, open-concept suite with a separate bedroom features unique artwork by Guelph artist Ryan Price. Located above a quiet RMT clinic, you'll enjoy a peaceful and private stay. Walking distance to trendy shops and cafes. Free parking is included for your convenience. Book now to experience a blend of comfort, art, and convenience!
4.95 out of 5 average rating, 197 reviews
The Fox's Retreat - A Cozy Cabin for Two
Escape to this open concept cabin in Flamborough, Ontairo. Get to Flamborough Downs Casino and Racetrack, McMaster University, African Lion Safari, Valens and Christie's Conversation Areas, Westfield Heritage Village, and Dundas Waterfalls and multiple Golf Courses in under 15 minutes. Modern amenities provide all the comforts necessary for a relaxing stay, quiet remote work, or a unique space to get wedding ready.
4.99 out of 5 average rating, 202 reviews
Luxurious 5BR Beach House with Firepit
Spatious and luxirious house by the beach has 5 bedrooms with a large comfy sectional, enough to sleep 10 guests total. Our kitchen is fully stocked with everything you need to make grand dinners. We have a beautiful long custom designed dining table for memorable family gatherings. Enjoy serene views of the lake on our large furnished deck, where there is a large BBQ, dining area, sofa, and fire table.
4.9 out of 5 average rating, 188 reviewsPopular amenities for Cockpit Island holiday rentals
Other great holiday rentals in Cockpit Island

The Bayfront - Harbour Views + Private Pool!
4.9 out of 5 average rating, 82 reviews
Beautiful modern 2Bdr sunny home with French decor
4.97 out of 5 average rating, 39 reviews
Spacious & Luxury 4BR Home ~ Hamilton ~ Comfort
4.84 out of 5 average rating, 38 reviews
Studio Near Gore Park & GO Station w Parking
4.79 out of 5 average rating, 94 reviews
Upscale Living 5BR 3BA | Near Ancaster Mill
4.89 out of 5 average rating, 92 reviews
Bright & Spacious 2 BR Apartment. Free Parking
4.95 out of 5 average rating, 22 reviews
Cozy 3BR Home w/ Kitchen + Parking | West Mountain
5.0 out of 5 average rating, 52 reviews
City Meets Forest Year Round Tree House Retreat
4.94 out of 5 average rating, 17 reviewsDestinations to explore
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- CN Tower
- Rogers Centre
- Scotiabank Arena
- University of Toronto
- Union Station
- Downsview Park
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Harbourfront Centre
- Niagara Falls
- Toronto Eaton Centre
- Niagara Falls State Park
- Scarborough Town Center
- Nike Square One Shopping Centre
- Exhibition Place
- Elora Gorge
- Yorkdale Shopping Centre
- Casa Loma
- Sheppard–Yonge Station
- Trinity Bellwoods Park
- York University
- The International Centre
- Enercare Centre
- Coca Cola Coliseum





